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Top 10 Best Hawaii Sailing Trips

Found 99 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 117 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb117 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 440 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb440 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 913 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb913 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $84.99
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 772 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $148.57
 
Sunset and Manta Ray Snorkel Adventure

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb772 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $148.57
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 26 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb26 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 702 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb702 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 55 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise

Pau Hana Sunset Cocktail Cruise

  • Hawaii
  • Superb55 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Start From $165.00
 
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 157 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $152.55
 
Sunset Sail Experience at Kona from Honokohau

Sunset Sail Experience at Kona from Honokohau

  • Hawaii
  • Superb157 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $152.55
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.9 of 221 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb221 reviews4.9

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 153 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • Hawaii
  • Superb153 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.8 of 247 reviews)

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Free Cancellation
Start From $99.00
 
Sail and Turtle Snorkeling Tour in Waikiki

Sail and Turtle Snorkeling Tour in Waikiki

  • Hawaii
  • Superb247 reviews4.8

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....

    Free Cancellation
    Start From $99.00
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 80 reviews)

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Free Cancellation
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb80 reviews4.9

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....

    Free Cancellation
    Start From $289.00
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 254 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Start From $96.30
 
9am Turtle Canyon Snorkel Adventure

9am Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb254 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Start From $96.30
 
 
-20% Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)

Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)

(4.9 of 254 reviews)

This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. Our Disco Sunset Party Cruise blends the thrill of ocean adventure with vibrant party energy. You’ll kick off the evening with ... More

Special Offer
Free Cancellation
Start From $71.20
(Saving 20% ) $89.00
 
-20% Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)

Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)

  • Hawaii
  • Superb254 reviews4.9

This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. ....

    Special Offer
    Free Cancellation
    Start From $71.20
    (Saving 20% ) $89.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui

  • Hawaii
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Start From $179.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 185 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Hawaii
  • Superb185 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Start From $49.99
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 208 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our  luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Start From $133.05
 
Sunset Sail from Ma'alaea Harbor

Sunset Sail from Ma'alaea Harbor

  • Hawaii
  • Superb208 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $133.05
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Start From $83.40
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Hawaii
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Start From $83.40
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 17 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests)

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Hawaii
  • Superb17 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

(4.8 of 36 reviews)

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Free Cancellation
Private Tour
Start From $117.76
 
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

  • Hawaii
  • Superb36 reviews4.8

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....

    Free Cancellation
    Private Tour
    Start From $117.76
 
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